TWI302534B - Method for preparation of 1-oxachephalosporin-7 α-methoxy-3-cloromethyl derivative - Google Patents

Method for preparation of 1-oxachephalosporin-7 α-methoxy-3-cloromethyl derivative Download PDF

Info

Publication number: TWI302534B
Authority: TW; Taiwan
Prior art keywords: compound; project; reaction; patent application; following formula
Prior art date: 2004-07-08

Application number

TW094122786A

Other languages

English (en)

Chinese (zh)

Other versions

TW200606167A (en

Inventor

Toshiro Konoike

Original Assignee

Shionogi & Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2004-07-08

Filing date

2005-07-06

Publication date

2008-11-01

2005-07-06 Application filed by Shionogi & Co filed Critical Shionogi & Co

2006-02-16 Publication of TW200606167A publication Critical patent/TW200606167A/zh

2008-11-01 Application granted granted Critical

2008-11-01 Publication of TWI302534B publication Critical patent/TWI302534B/zh

Links

238000000034 method Methods 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims description 51
238000006243 chemical reaction Methods 0.000 claims description 28
239000003795 chemical substances by application Substances 0.000 claims description 18
230000002140 halogenating effect Effects 0.000 claims description 15
239000002585 base Substances 0.000 claims description 9
229910052783 alkali metal Inorganic materials 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 6
238000005755 formation reaction Methods 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 4
125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
238000010511 deprotection reaction Methods 0.000 claims description 3
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
238000005886 esterification reaction Methods 0.000 claims description 2
150000002923 oximes Chemical class 0.000 claims description 2
235000010265 sodium sulphite Nutrition 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
229910052736 halogen Inorganic materials 0.000 claims 3
150000004982 aromatic amines Chemical class 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
238000006481 deamination reaction Methods 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical group [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims 1
235000019345 sodium thiosulphate Nutrition 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000543 intermediate Substances 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 4
239000012295 chemical reaction liquid Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229940125898 compound 5 Drugs 0.000 description 3
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 3
238000006198 methoxylation reaction Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
-1 hydrazone compound Chemical class 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
LSCYTCMNCWMCQE-UHFFFAOYSA-N n-methylpyridin-4-amine Chemical compound CNC1=CC=NC=C1 LSCYTCMNCWMCQE-UHFFFAOYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003760 tallow Substances 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

TW094122786A 2004-07-08 2005-07-06 Method for preparation of 1-oxachephalosporin-7 α-methoxy-3-cloromethyl derivative TWI302534B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2004201578A JP3771566B2 (ja)	2004-07-08	2004-07-08	１−オキサセファロスポリン−７α−メトキシ−３−クロルメチル誘導体の製法

Publications (2)

Publication Number	Publication Date
TW200606167A TW200606167A (en)	2006-02-16
TWI302534B true TWI302534B (en)	2008-11-01

Family

ID=34792648

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW094122786A TWI302534B (en)	2004-07-08	2005-07-06	Method for preparation of 1-oxachephalosporin-7 α-methoxy-3-cloromethyl derivative

Country Status (5)

Country	Link
EP (1)	EP1767538B1 (ja)
JP (1)	JP3771566B2 (ja)
CN (1)	CN1980939B (ja)
TW (1)	TWI302534B (ja)
WO (1)	WO2006006290A1 (ja)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103183686B (zh) *	2011-12-30	2016-06-29	浙江新和成股份有限公司	7β-氨基-7α-甲氧基-3-头孢烯化合物的制备方法
CN103183688B (zh) *	2011-12-30	2016-01-20	浙江新和成股份有限公司	7β-酰胺基-7α-甲氧基-1-氧代-3-头孢烯化合物的制备方法
JP2015524426A (ja) *	2012-07-25	2015-08-24	ジェイルファルマシューティカルシーオー．，エルティーディー．ＪｅＩｌＰｈａｒｍａｃｅｕｔｉｃａｌＣｏ．，Ｌｔｄ．	１−オキサセファロスポリン誘導体の新規な製造方法
CN102952149B (zh) *	2012-11-09	2015-06-24	浙江新和成股份有限公司	一种氟氧头孢中间体的一锅合成法
CN104610278A (zh) *	2015-01-09	2015-05-13	郑州大学	一种氧头孢烯类抗生素中间体亚砜酯的安全生产方法
CN105037393B (zh) *	2015-06-24	2017-11-10	浙江永宁药业股份有限公司	一种氟氧头孢钠的制备方法
CN105399755B (zh) *	2015-11-03	2018-05-11	浙江永宁药业股份有限公司	一种氟氧头孢酸的合成方法
CN106188097B (zh) *	2016-07-08	2018-01-05	郑州大学	一种3‑氯甲基氧头孢烯类抗生素母核的制备方法
CN106749335B (zh) *	2016-11-29	2019-02-12	浙江新和成股份有限公司	一种卤代氧头孢类中间体的制备方法和应用
CN107118224B (zh) *	2017-06-15	2019-09-17	浙江新和成股份有限公司	一种氧头孢母核中间体的制备方法、其溶剂化合物及其制备方法
KR102115644B1 (ko) *	2017-09-13	2020-05-27	주식회사 동도물산	7α-알콕시옥사세펨 중간체의 제조방법
CN109485660A (zh) *	2018-12-21	2019-03-19	齐鲁安替制药有限公司	一种氧头孢母核的合成方法
CN110003242A (zh) *	2019-04-23	2019-07-12	山西千岫制药有限公司	一种氟氧头孢酸杂质标准品的制备方法
CN110003241A (zh) *	2019-04-23	2019-07-12	山西千岫制药有限公司	一种拉氧头孢母核的制备方法
CN114805395B (zh) *	2022-04-27	2023-03-28	陕西友帮生物医药科技有限公司	一种氧头孢烯母核中间体的制备方法
CN116496298A (zh) *	2023-05-04	2023-07-28	深圳六合六医疗器械有限公司	一锅法制备氟氧头孢中间体的方法
CN116813644A (zh) *	2023-05-19	2023-09-29	广东立国制药有限公司	一种氟氧头孢母核的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4604460A (en) *	1977-02-15	1986-08-05	Shionogi & Co., Ltd.	1-oxadethiacepham compounds
JPS53101391A (en) *	1977-02-15	1978-09-04	Shionogi & Co Ltd	1-oxadithiacephem compounds
JPS5967289A (ja)	1982-10-08	1984-04-16	Shionogi & Co Ltd	Ｎ−ハロアシルアミノオキサセフアム誘導体
JPS61246187A (ja) *	1985-09-05	1986-11-01	Shionogi & Co Ltd	１―オキサデチアセファム化合物の製造方法

2004
- 2004-07-08 JP JP2004201578A patent/JP3771566B2/ja not_active Expired - Fee Related
2005
- 2005-04-20 CN CN2005800230055A patent/CN1980939B/zh not_active Expired - Fee Related
- 2005-04-20 EP EP05734618.1A patent/EP1767538B1/en not_active Expired - Lifetime
- 2005-04-20 WO PCT/JP2005/007517 patent/WO2006006290A1/ja not_active Ceased
- 2005-07-06 TW TW094122786A patent/TWI302534B/zh not_active IP Right Cessation

Also Published As

Publication number	Publication date
CN1980939B (zh)	2012-05-30
JP3771566B2 (ja)	2006-04-26
CN1980939A (zh)	2007-06-13
EP1767538A4 (en)	2010-04-28
JP2005179336A (ja)	2005-07-07
EP1767538B1 (en)	2014-05-07
WO2006006290A1 (ja)	2006-01-19
EP1767538A1 (en)	2007-03-28
TW200606167A (en)	2006-02-16

Legal Events

Date	Code	Title	Description
2018-08-01	MM4A	Annulment or lapse of patent due to non-payment of fees

Publication	Publication Date	Title
TWI302534B (en)	2008-11-01	Method for preparation of 1-oxachephalosporin-7 α-methoxy-3-cloromethyl derivative
US10358423B2 (en)	2019-07-23	Processes for the preparation of 4-alkoxy-3-(acyl or alkyl)oxypicolinamdes
US11820752B2 (en)	2023-11-21	Process for the preparation of apalutamide
EP1132391B1 (en)	2006-11-15	Process for the preparation of 3-sulfonyloxy-3-cephem compounds
JPH01258684A (ja)	1989-10-16	３‐置換キノリニウムチオメチルセファロスポリン誘導体
KR100899325B1 (ko)	2009-05-26	1-옥사세팔로스포린-7α-메톡시-3-클로로메틸 유도체의제조 방법
JPH11124384A (ja)	1999-05-11	３−セフェム化合物の製造法
JP5234856B2 (ja)	2013-07-10	Ｎｐｙｙ５受容体拮抗作用を有する化合物の結晶
US4304909A (en)	1981-12-08	Process for producing 7-(D(-)-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-α-(4-hydroxyphenyl)acetamido)-3-(5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl)-.DELTA.3 -cephem-4-carboxylic acid and a pharmaceutically acceptable salt thereof
JP4675234B2 (ja)	2011-04-20	光学活性なキノロンカルボン酸誘導体の製造中間体およびその製造法
JP4659959B2 (ja)	2011-03-30	３−セフェム化合物及びその製造法
JP2525170B2 (ja)	1996-08-14	２―オキサイソセフェム誘導体の製造方法
CN105585580A (zh)	2016-05-18	甲氧头孢类药物中间体7-mac的合成方法
CN104163803B (zh)	2017-01-04	一种头孢洛林酯的合成方法
JP2004149412A (ja)	2004-05-27	７−［２−（２−アミノチアゾール−４−イル）−２−低級アルコキシカルボニルメトキシイミノアセトアミド］−３−セフェム化合物の製造法
JP3775820B2 (ja)	2006-05-17	ハロゲン化β−ラクタム化合物の製造法
JPH08245635A (ja)	1996-09-24	２−イソセフェム誘導体の製造法
JP3791941B2 (ja)	2006-06-28	３−ハロゲン化セフェム誘導体の製造法
JPS61271285A (ja)	1986-12-01	チオフエノン誘導体およびその製造法
JP2000247970A (ja)	2000-09-12	５−アミノ−８−メチル−７−ピロリジニルキノリン−３−カルボン酸誘導体の製造法及びその製造中間体
JPS6343399B2 (ja)	1988-08-30
KR20040006205A (ko)	2004-01-24	아즈트레오남의 신규제조방법
JPH0578371A (ja)	1993-03-30	７−アミノ−３−クロロメチル−３−セフエム誘導体の製法
WO2006077919A1 (ja)	2006-07-27	イミダゾチアゾール誘導体およびその製造方法
JPH0517229B2 (ja)	1993-03-08